Fragmentation of nitrone triflates to 9-membered rings

John A. Murphy, Mohan Mahesh, Gary McPheators, R. Vijaya Anand, Thomas M. McGuire, Robert Carling, Alan R. Kennedy

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

LanguageEnglish
Pages3233-3236
Number of pages4
JournalOrganic Letters
Volume9
Issue number17
DOIs
Publication statusPublished - 16 Aug 2007

Fingerprint

fragmentation
rings
Cyclization
Amides
Electrons
Oxygen
Derivatives
anhydrides
amides
nitrones
oxygen
electrons
triflic anhydride

Keywords

  • nitrone triflates
  • cyclization
  • amides

Cite this

Murphy, J. A., Mahesh, M., McPheators, G., Anand, R. V., McGuire, T. M., Carling, R., & Kennedy, A. R. (2007). Fragmentation of nitrone triflates to 9-membered rings. Organic Letters, 9(17), 3233-3236. https://doi.org/10.1021/ol071049d
Murphy, John A. ; Mahesh, Mohan ; McPheators, Gary ; Anand, R. Vijaya ; McGuire, Thomas M. ; Carling, Robert ; Kennedy, Alan R. / Fragmentation of nitrone triflates to 9-membered rings. In: Organic Letters. 2007 ; Vol. 9, No. 17. pp. 3233-3236.
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Murphy, JA, Mahesh, M, McPheators, G, Anand, RV, McGuire, TM, Carling, R & Kennedy, AR 2007, 'Fragmentation of nitrone triflates to 9-membered rings' Organic Letters, vol. 9, no. 17, pp. 3233-3236. https://doi.org/10.1021/ol071049d

Fragmentation of nitrone triflates to 9-membered rings. / Murphy, John A.; Mahesh, Mohan; McPheators, Gary; Anand, R. Vijaya; McGuire, Thomas M.; Carling, Robert; Kennedy, Alan R.

In: Organic Letters, Vol. 9, No. 17, 16.08.2007, p. 3233-3236.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Fragmentation of nitrone triflates to 9-membered rings

AU - Murphy, John A.

AU - Mahesh, Mohan

AU - McPheators, Gary

AU - Anand, R. Vijaya

AU - McGuire, Thomas M.

AU - Carling, Robert

AU - Kennedy, Alan R.

PY - 2007/8/16

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AB - A new fragmentative rearrangement of nitrone derivatives to form 9-membered rings is reported. The fragmentations are triggered when nitrones are treated with triflic anhydride; a C-C bond antiperiplanar to the cleaving N-O bond is activated either by an oxygen lone pair or by an electron-rich aromatic ring. In the former case, further cyclization of the 9-membered intermediate leads to a rearranged condensed ring system, but when triggered by arenes, 9-membered ring amides are isolated.

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KW - cyclization

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Murphy JA, Mahesh M, McPheators G, Anand RV, McGuire TM, Carling R et al. Fragmentation of nitrone triflates to 9-membered rings. Organic Letters. 2007 Aug 16;9(17):3233-3236. https://doi.org/10.1021/ol071049d